Galatasaray AŞ lost 5-0 in Chelsea FC's previous visit, though they now have inside knowledge of Didier Drogba, a UEFA Champions League winner with the Blues in 2012.
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Chelsea FC's only previous visit to Galatasaray AŞ ended in a 5-0 win and now one of their former heroes will be looking to prevent a repeat when the teams meet in the round of 16 first leg.
• Didier Drogba was part of the Chelsea side that lifted the UEFA Champions League for the first time in 2011/12, scoring a late equaliser and then the decisive penalty in the final shoot-out against FC Bayern München in Munich on 19 May 2012. That was the Ivorian's final kick for the club.
• This season Chelsea made up for their 2012/13 disappointment, when they became the first UEFA Champions League holders to fail to make it through the group stage. That failure was the only blot in 11 otherwise consecutive qualifying campaigns; this season, José Mourinho's side won their group for the eighth time in that span.
• Mourinho masterminded Chelsea's sole round of 16 defeat between 2006/07 and 2011/12, as coach of FC Internazionale Milano in 2009/10.
• Although they reached the second group stage in 2000/01 and again the following year, Galatasaray's only previous experience of the round of 16 came last year when they beat FC Schalke 04 4-3 on aggregate. The home leg ended 1-1, Burak Yılmaz opening the scoring. Hamit Altıntop and Burak were on target in the away game, substitute Umut Bulut firing the winner.
• Tore André Flo gave Chelsea a two-goal cushion in the UEFA Champions League group stage fixture between the teams 15 years ago by scoring either side of the interval. Further second-half goals arrived from Gianfranco Zola and substitutes Dennis Wise and Gabriele Ambrosetti.
• The lineups in the Ali Sami Yen Spor Kompleksi on 20 October 1999 were:
Galatasaray: Mehmet Bölükbasi, Popescu, Emre Belözoğlu, Arif Erdem, Okan Buruk, Fatih Akyel (Ümit Davala 46), Hagi (Hasan Şaş 46), Tugay Kerimoğlu, Hakan Ünsal, Hakan Şükür (Saffet Akyüz 65), Capone.
Chelsea: De Goey, Ferrer, Leboeuf, Desailly, Le Saux, Deschamps (Wise 66), Morris, Poyet (Petrescu 66), Babayaro, Flo, Zola (Ambrosetti 75).
• The game in London on 28 September 1999 had ended 1-0 to Chelsea with Dan Petrescu (52) on target.
• That home defeat was the second suffered by Galatasaray in eight games at home to English opponents. With wins in both their last two encounters – in the group stage against Liverpool FC in 2006/07 (3-2) and Manchester United FC (1-0) last season – their home record is W3 D3 L2. Overall it is W3 D7 L7.
• In 1999/2000 Galatasaray defeated Arsenal FC 4-1 on penalties after the UEFA Cup final in Copenhagen had finished goalless following extra time, becoming the first Turkish team to win a UEFA competition.
• In their last meeting with a Turkish club, Chelsea lost 2-1 at Fenerbahçe SK in the 2007/08 quarter-finals, but won 2-0 at home to progress. They also met Beşiktaş JK in the 2003/04 group stage, losing 2-0 at Stamford Bridge but won by the same scoreline in the away game, at the Arena AufSchalke in Gelsenkirchen, Germany.
• Galatasaray lost their first game in Group B 6-1 at home to Real Madrid CF, Roberto Mancini subsequently replacing Fatih Terim as coach and overseeing a draw at Juventus in his first game on matchday two. The point would prove crucial as the Turkish side defeated Juve on matchday six through Wesley Sneijder's late goal to finish runners-up in the section.
• In their other home game, Galatasaray beat FC København 3-1 but lost in Copenhagen (0-1) and Madrid (1-4).
• Chelsea, looking to win a European trophy for the third successive year after capturing the UEFA Champions League in 2012 and the UEFA Europa League in 2013, won Group E by a two–point margin from Schalke despite home-and-away defeats against FC Basel 1893. They won all four other fixtures without conceding a goal, beating FC Steaua Bucureşti 4-0 away and 1-0 at home and Schalke 3-0 home and away.
• Mourinho, who has captured the UEFA Champions League with both FC Porto (2004) and FC Internazionale Milano (2010), is bidding to become the first manager to win the European Cup with three different teams. Only Bob Paisley (Liverpool FC 1977, 1978, 1981) has won the trophy three times as a coach.
• Drogba was at Chelsea between 2004 and 2012 – playing under Mourinho from June 2004 to September 2007 – and scored 100 goals in 226 league matches. He also won three Premier League titles, four FA Cups and two League Cups.
• Emmanuel Eboué was at Arsenal FC between 2005 and 2011, playing alongside Ashley Cole until 2006.
• Mancini was manager of Manchester City FC from December 2009 to May 2013, leading them to the Premier League title in 2011/12. He also won the 2011 FA Cup with the club.
• Sneijder played under Mourinho at Inter in 2009/10, helping eliminate Chelsea 3-1 on aggregate in the round of 16 on their way to lifting the trophy.
• Altıntop played for Mourinho at Real Madrid CF in 2011/12.
• Felipe Melo and Ramires were in the Brazil squad at the 2009 FIFA Confederations Cup and 2010 FIFA World Cup.